


Exploring

by discount67



Series: A Series Of Fortunate Events [1]
Category: Supernatural
Genre: First Orgasm, M/M, Masturbation, Mutual Masturbation, Sexuality Crisis, Smut, Voyeur Sam Winchester, Voyeurism
Language: English
Status: Completed
Published: 2020-07-16
Updated: 2020-07-16
Packaged: 2021-03-05 01:34:46
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,420
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25306084
Author URL: https://archiveofourown.org/users/discount67/pseuds/discount67
Summary: Sam has been lusting over Jack, and his dreams come true when he gets caught in a compromising situation. Jack learns about self-gratification and sexuality.
Relationships: Jack Kline & Sam Winchester, Jack Kline/Sam Winchester
Series: A Series Of Fortunate Events [1]
Series URL: https://archiveofourown.org/series/1841971
Comments: 5
Kudos: 51





	Exploring

Jack liked doing research, eager to help with what Sam and Dean were up to next. He wasn't allowed to come with them often, but he was content working from the bunker. Whenever Jack came up with a workable lead Sam would compliment him, telling him he did a great job. Dean would award the boy with an affectionate nickname. Jack basked in the glory of it all, he looked up to these guys and their approval meant everything.

Sam and Jack were once again sitting around the table, scrolling through articles as they dug up information on a streak of mysterious disappearances. Dean was checking out the site with Castiel. They often called to check in on Jack, asking him what he did today and if he missed them. Jack always missed Castiel, glad when he got to welcome him home.

Jack grasped his pen, occasionally taking notes when he came across something interesting. Twirling the ball point between his fingers caught Sam's attention. The clinking of the metal brought him out of his focus, but it didn't seem to bother Jack.

Sam slid his hand forward across the table to catch Jack's attention. “Hey bud, could you stop doing that?” Jack's head shot up, realizing that he was now tapping the pen on the table. He nodded absentmindedly, head buzzing with the stories he had been sifting through. “Sorry. Just focused s'all.” Jack muttered. He lifted the pen and rested the tip of it between his lips. Sam smiled at him, eyes lingering a little too long on those lips.

The younger Winchester truly adored Jack, that gap-toothed grin filled his heart with joy. He had been there for Jack the first time he had a fever, the first time laughing so hard he couldn't breathe, the first time he cried and cursed at the world for being so overwhelming. Jack's whole being screamed innocence, yet Sam couldn't deny his feelings for the Nephilim were darker than they used to be. Sam eyed the way Jack chewed on the top of his pen, slick lips working along the metal. 

He and Dean gave Jack his space when he first settled in the bunker, allowing him to retreat into his room to get accustomed to life. It hadn't been long until he moved on to indulge in the more pleasurable experiences life had to offer. Jack didn't need to eat very often, however he jumped at the chance to sneak a little of whatever Dean was having off to his room, grinning widely as he ran off to escape from Dean's grasp. He didn't need to shower, but he loved the feeling of hot water against his skin. Jack loved how his body reacted to touches, innocently playing with himself at night. He would scratch and pinch at his sensitive skin, tiny moans escaping his lips. Goosebumps raised on Sam's skin as he remembered a particular night.

***

Late at night strange feelings in the Nephilim's belly kept him awake. Blood rushed to his head, rendering his skin flushed. The touch of his sheets felt like too much and soft sighs escaped his mouth as his body tingled all over. An itch awakened between Jack's thighs and he held back a strained sound as he rubbed them together. Jack shoved his blanket back, he needed cold air to combat the heat his body was producing, but the cool sensation stimulated him even more. He let a hand run down to his thighs to explore the unusual feeling, humming when sparks of pleasure shot through his groin. Jack's member hardened and his eyes widened at the sight. Was it okay to touch it? Maybe Sam would know. 

Unbeknownst to Jack, Sam was already aware of the situation. He had just gotten ready for bed, hair still wet from the shower when he picked up on a quiet groan. Concern grew in his stomach as he went over to Jack's bedroom door. It was partly open. Sam raised his hand to knock, but another sigh stopped him in his tracks. It didn't sound like Jack was in pain. Realisation hit Sam, and he grinned to himself. It looked like Jack discovered the wonders of self pleasure.

He did his best to stop himself from peeking inside the room, but he couldn't resist. Jack was such a pretty boy, so expressive. Sam needed to see his face. Breathing heavily, he pushed the door a bit farther open to see Jack all sprawled out on the bed. 

Jack bit down on his finger as he rubbed the front of his boxers. His bright golden eyes were the only things lighting up the room. He tilted his head back and his toes were curled, indicating how good it felt. Sam felt himself getting painfully hard at the sight of the young man. He watched until Jack's movements slowed down along with his breathing. Jack nodded off without finishing what he started. Sam's legs were trembling slightly from watching this angelic boy do something so dirty. A pang of guilt hit him. What would Cass think? 

***

“Sam? Sam!” Jack shouted, waving his hand in front of Sam's face. Sam squeezed his eyes shut to get back to reality. He smiled hesitantly, cringing inwardly as the sight of Jack pleasuring himself had not yet left his mind. He shifted uncomfortably in his chair, realizing he had an erection. If only Jack knew. If only Cass knew. God, he would have been smitten on sight.

“What's the matter?” Sam asked, expression softening from seeing Jack's smiling face.

“Can we stop for tonight? It's late and I wanted to finish the movie.” Jack asked.

“Sure, Jack. I'll text Dean about what we found today, make sure he tells Cass to call you.” Sam smiled as Jack's eyes lit up at the mention of his caretaker. The boy loved Castiel very much, he was satiated with the promise of talking to him later. Jack left the study to go to his own room.

Sam froze in his spot until he was sure he heard Jack's bedroom door clicking shut. With a sharp exhale he pushed himself away from the table, the tent in his jeans now painfully visible. Now Jack, Dean and Cass weren't around there was no harm in relieving himself right on the spot. Sam gasped as he undid his zipper, boxer-clad hardness springing loose. With the constriction of his tight pants out of the way Sam ran a finger along the underside of his cock. This motion earned the empty room a stifled groan, Sam's hips bucked up into the air. Normally Sam would take his time to undress himself slowly, stimulating his sensitive skin before giving himself the first tug. This time he couldn't wait, Jack had awakened something so primal in him, he pushed his boxers down right away. 

Sam's cock slapped against his stomach, a bead of pre-come already collecting at the tip. Everything about Sam was large, his cock was no exception. It felt heavy and hot in his hand, the veins visible under the tanned skin. He gave himself a short experimental stroke, his jaw fell slack as a rather loud moan escaped his throat.

His mind was hazy with thoughts of the Nephilim, eyes of gold burned at the back of his mind. Sam wrapped his hand around himself a little tighter and began a steady rhythm, making small sounds with every tug at his hardness. He let his head fall back, thrusting into his hand. Down the hallway a door cracked open, footsteps going unnoticed by Sam. 

“Hey, did you text-” Jack's eyes widened as he stopped in his tracks. “Oh. Um, sorry.” A murmured apology was all that came out, yet Jack did not leave or turn around to let Sam make himself decent. Sam scrambled at the edge of the table to cover himself up, cursing all the while.

“Shit, Jack, turn around,” Sam hissed. His face heat up from embarrassment. He didn't mean to expose himself like this, he truly thought he could finish before anyone got back. Jack turned around as Sam tucked himself back into his pants. “I'm sorry you had to see that. I thought you were going to watch a movie?” Sam apologized. Jack turned back around, cheeks tinged pink after having seen Sam in such a compromising position. 

“I am, I was just going to grab a snack first,” he said. Sam groaned, hiding his face behind his hands. “You don't have to be embarrassed, I do it too,” Jack said bluntly. He tilted his head like something was on his mind. “I didn't know that's how you're supposed to do it though.” Sam's eyes nearly bulged out of his head. Jack could be very direct, but this was a whole new level of direct. All Sam wanted to do was to call Jack over and show him how it's done, but he felt morally inclined to bring up Castiel.

“Wow. Uh, I think you should talk to Cass about this.” Sam offered. He tried his best to not get too personal with Jack, certain things are best left answered by his caretaker. He had no idea if Jack understood what consent was, and he would never manipulate the younger man into doing something sexual.

Jack giggled. “Dean says Castiel is a prude.” Sam stifled a laugh. That sounded like something Dean would say. 

“He kind of is. I would explain everything but I don't think it's appropriate.” Sam said. He scrambled for the laptop on the table, opened internet and typed something in the search bar. “Here, learn about it yourself.” He handed the device to Jack.

“Masturbation?” Jack's eyes slid across the screen. He awkwardly shifted on his feet. Sam noticed he an erection as well. 

Sam nodded. “Yeah. Read about it, or watch some videos.” Jack hesitantly looked at the screen, and set the laptop back down.

“Sam, I don't like the videos. I borrowed Dean's laptop once.” Sam could imagine this traumatized the poor boy. Dean wasn't particularly vanilla when it came to porn.

“That's okay. Do you know if you like women or men?”

“I like you and Dean and Castiel.” Jack said innocently, not realizing the bond he had with the three made this completely inappropriate. Sam's heart swelled with pride, he was happy Jack loved him so much, but it made it all the more bitter. 

“I like you too, Jack, but that's not what I meant,” Sam can't seem to say the words, so he hinted towards what he meant. “What do you think about when you're alone at night?”

“Ah, when I do masturbation?” Jack asked. He didn't even know how to say it right, it was so innocent yet vile at the same time.

“It's just 'masturbate', Jack.” Sam corrected.

Jack nodded. “I think about someone else touching me,” He almost whispered it. He didn't dare confess he usually thought of strong hands and stubble and tight abs. He wasn't sure what that meant yet. He knew Dean and Sam liked women, so maybe he wasn't supposed to dream about men. He wouldn't want them to think of him differently, especially Castiel.

Jack's cheeks were bright red. “I can't seem to do what the people in Dean's videos do,” Sam's mind rewinded to the moment he saw Jack fall asleep without orgasming, and realized the boy must have never come before. The fact he'd never experienced such bliss before was unacceptable. It looked like Jack only palmed his erection instead of actually jerking off. “What's wrong, Sam?”

Sam sighed, having made up his mind about what he was going to offer. “Jack, I would never hurt you or do something you don't wanna do. If I'm going to show you I need your consent.” 

Frowning, Jack recalled a conversation he had with Cass. He sat Jack down before to have a one on one. “There are a lot of things in the world you're going to experience one day,” Cass told him. “Things you shouldn't rush. You don't have do things you're not ready for.” Jack understood, he had to wait until he was ready to hunt. Thinking back, it applied to this situation as well.

Jack looked Sam in the eyes, nodding firmly. “Castiel told me to never do something I don't want to do. I understand.” Sam exhaled shakily, realising this was really about to happen. He motioned for Jack to sit down in front of him.

Sam unzipped his jeans again. “Ready?” He asked, pulling his underwear down instantly when Jack nodded. His cock stood up fierce just like before, the head an angry red color. It begged for stimulation, but Sam didn't want to give in yet. Jack's eyes were fixated on Sam, wiggling in his chair as his erection got uncomfortable. 

“It's okay, Jack. You can take yours out too.” Sam said, glancing at the obvious tent in Jack's pants. Jack did as he was told, exhaling sharply as his hardness slipped out of his boxers. “You still okay? We can stop at any time.” Sam reassured him. Jack smiled and nodded softly, feeling at ease with Sam. He trusted the older man with his life.

Jack's cock matched his posture, not very wide around but definitely impressively sized. The head was weeping pre-come, and Sam saw his pelvic muscles flex. Jack looked up at Sam, awaiting instructions. “It's hard.” He stated the obvious.

“Yeah, it is.” Sam said. Deep within he wanted to touch Jack, but he wouldn't dare hurt this boy. They were only going to watch each other until Jack says he's ready to do more. Sam cleared his throat, staring into Jack's expectant eyes. “We're not going to touch each other, okay? Just follow what I'm doing.” Jack nodded again.

Sam slipped his hand between his thighs, caressing himself gently so Jack could follow his lead. Jack's breath hitched in his throat as he repeated after Sam. Both guys' fingers were travelling across their body's, one hand cupping their balls as the other slid up their torso's. Sam and Jack groaned in unison, the older man closed his eyes to fully appreciate the sensation. Jack's eyes were still on Sam, watching his experienced hands working. “You got it?” Sam asked breathily.

“Yes… it's good.” Jack breathed, he allowed himself to finally close his eyes. He continued to pet his sensitive spots, nails raking up and down his sides. His breathing was getting ragged, and his cock was begging for attention. “Sam, I need to touch it.”

Sam's eyes shot open and he took in the sight of the angelic boy pistoning his hips in the air. He looked beautiful, his face and neck were blotchy and his eyes half-lidded. Sam grew hungry at the sight, giving in to Jack's plea. “Show me how you touch yourself.” He instructed. He watched how Jack palmed his erection gently.

Jack sighed, content with the skin on skin contact, but Sam had other ideas. “Hey, try to wrap your hand around it.” he guided, giving Jack a second to adjust. Jack's hand slid down to the base of his erection, curling his fingers around it. Sam was awarded with a loud gasp. Jack's sighs of pleasure encouraged Sam to do the same to himself. “Feel better?” He asked.

Groaning, Jack rapidly nodded his head. “Oh. Oh, much better,” his moans increased as he tightened his hand around his cock. “More, more.” He moaned breathlessly.

“Good job, Jack. You're doing great,” Sam praised, his eyes almost rolled back at the erotic show Jack was putting on in front of him. “Move your hand up and down,” he said, biting his lip as Jack gently pumped himself. “Yeah, just like that.” Sam encouraged him. He stroked his cock, matching Jack's speed.

Jack's jaw fell slack, gentle moans slipping from his lips uncontrollably. “Sam, Sam, ah. Ah-” he cried out. His legs tensed up as he picked up the speed. Jack was inching off the chair, overstimulating himself. Sam wanted Jack's first orgasm to be earth-shattering but the boy couldn't be straining like this, he'll wreck himself. He needed to slow down but Jack's delicious moans were like fuel for Sam, bucking up in his hand with every cry of his name.

“Christ, Jack. You're amazing,” Sam moaned. “You have to relax, take it slow.” Jack stretched and let the tension flood from his body as he slowed down. “Good boy, don't overwork yourself.” Jack shuddered at the praise and mimicked the way Sam stroked himself. He ran his thumb over the slit of his cock, exhaling sharply at the sensation. Sparks shot through his lower body, and strange feeling washed over him. It felt like hunger, or maybe thirst. A desire that needed to be quenched.

Sam groaned loudly, head thrown back and mouth agape. Jack found him beautiful like this. Jack sped up the movement of his fist, his other hand covering his mouth to silence his moans. “Don't. I want to hear you.” Sam said. Jack hummed in response and removed his fingers from his lips to let the sounds flow freely.

“I can't…” Jack breathed exaspiratedly, his back arched when his finger slid across his frenulum. He nearly keeled from the overwhelming pleasure, but couldn't seem to get any relief. “It won't come, Sam. It feels so-” Jack trailed off, hot tears filling his eyes.

Sam grunted as he fondled his balls, working his foreskin over the head of his cock. “It will, Jack, don't worry. Just look at me and focus on how it feels,” Sam said reassuringly. “It feels good, right?” Jack nodded, panting as he took in how Sam pleasured himself.

“Mm, it does. Oh, Sam.” Jack sighed, eyes rolling back as pleasure shot through his belly. He needed to come but he wasn't quite there yet. Sam was on the brink of orgasm already, biting his lip violently as he stroked his cock. His breathing sped up and his moans became louder. 

“Fuck. Fuck, oh my god. I'm close,” Sam groaned, opening his heavily lidded eyes to watch how Jack played with himself. The rosy cheeks and glowing eyes of the Nephilim drove him crazy like nobody else ever had managed before. Sam's stomach contracted. “Jack, yes, I'm-” Sam choked out, calling out Jack's name over and over again as he reached his high.

Sam's legs spasmed and his hips shot upwards as come spurted onto his stomach. The sight of Sam's bliss brought Jack closer to the edge. He observed the way come squirted onto Sam's tan skin, the way the muscles in this thighs flexed so deliciously, and the sounds that came from his throat. Jack fisted his cock quickly, letting his other hand slip down to squeeze his balls. Jack cried out as he felt an unfamiliar heat pool in his stomach, ready to explode.

Sam was still riding out his orgasm but he noticed Jack was close. “Be good for me and come, Jack. Come for me.” He encouraged. The praise was all Jack needed to come undone, warmth exploded in his body and he inched off his chair. He tipped his head back as he felt electricity surge through him, shaking him to the core. Every fiber in his body rippled with pleasure and Jack cried out Sam's name as he had his first orgasm. His back arched as his come shot up in the air, covering the hand that was still tugging on his cock.

Jack's eyes brightened as lights flickered in the room, a shadow of his wings casted onto the wall. Sam moaned at the sight, he was in awe at the intensity of Jack's orgasm. Cursing and panting, Jack came down from his high, still lazily rubbing his softening cock. His eyes turned back to their normal state and he looked into Sam's eyes.

“Are you going to say anything?” Sam asked jokingly after a minute of silence.

“That was… better than expected,” Jack said. Sam couldn't hold back his chuckle, even in the most intimate situations Jack replied so innocently. Jack had to get it off his chest. “I think I know for sure now.”

Sam took off his shirt to wipe up the come from his stomach. “Know what?” Jack caught the shirt Sam threw him midair, and cleaned himself up as well.

“I'm pretty sure I like men.”

Sam grinned at the younger man. “That's okay, buddy. And very convenient.”


End file.
